Alicyclic compounds each having a ring combined with a hydroxyl group are used, for example, as monomers or materials thereof for use in photosensitive resins and other functional polymers, and as intermediates of pharmaceuticals. Likewise, 5-hydroxy-2-adamantanone having an adamantane ring combined with a hydroxyl group is expected to be used as a monomer or a material thereof for use in resist resins, taking advantage of its unique cyclic structure.
Japanese Unexamined Patent Application Publication No. 9-327626 discloses a process for oxidizing adamantane with molecular oxygen by catalysis of a specific imide compound or of the imide compound and a metallic compound (refer to examples). However, the yield of 5-hydroxy-2-adamantanone having a hydroxyl group and an oxo group on an adamantane ring is very low according to this process, although adamantanol and adamantanepolyols can be obtained in good yields.